1H-PYRROLO[2,3-B]PYRIDIN-5-YLAMINE

Brown crystalline powder

To a stirred solution of 5nitro7azaindoie (500 rng, 3.07 rnmol) in methanol (125 rnL) under nitrogen atmosphere was added 10percent Pd/C (326 mg, 0.306 rnmol). The reaction was placed under an atmosphere of hydrogen gas and stirred at 20 °C overnight. The suspension was filtered through a pad of Celite® 545, the resulting filter cake was washed with MeOH, and the combined organicphases concentrated in vaeuo to afford the title compound (408 mg, 100percent). MS (ES1): mass calcd. for C7HN3 133.1, rn/z found 133.9 [M+H]t. ‘H NMR (300 MHz, DMSO-d6) ö 11.04 (s, 1H), 7.70 (d, J= 2.4 Hz, iH, 7.27 —7.18 (m, 1ff), 7.08 (d, J= 2.3 Hz, IH), 6.22 —6.06 (m, 1H), 4.62 (s, 2H).To a solution of 5-nitro-1H-pyrrolo[2, 3-b]pyridine (0.4 g, 2.45 mmol) in ethyl acetate (100 mL) 5percent Pd-C (0.3 g) was added and the mixture subdued to hydrogenation (30 psi) in a Parr apparatus. After 4 hours the catalyst was filtered off through celite, the cake was washed with ethyl acetate and then with a mixture of dichloromethane/methanol 4:1. 1H-pyrrolo[2, 3-b]pyridin-5-amine (5-aminoazaindole) was obtained in 95percent yield (0.31 g, 2.33 mmol). [Show Image]; (E)-3-(5-Phenylacetylamino-1H-pyrrolo[2, 3-b]pyridin-3-yl)-acrylamide; Step 1; 4 gr. (25 mmole) of 5-nitroazaindole (registry number 101083-92-5) were dissolved in 500 ml of ethanol and 150 ml of tetrahydrofuran and hydrogenated with a Parr apparatus after addition of 2 gr of Pd/C 10percent in 2 hrs. After filtration through a plug of celite and recrystallization from toluene/dicloromethane 3 gr of pure 5-aminoazaindole (1) were obtained (90percent yield). 1H NMR (400 MHz, DMSO-D6) δ ppm 4.62 (s, 2 H) 6.17(dd, J=3.29, 1.95 Hz, 1 H) 7.10 (dd, J=2.50, 0.55 Hz, 1 H) 7.24 (t, J=2.87 Hz, 1 H) 7.72 (d, J=2.56 Hz, 1 H) 11.04 (s, 1 H )[0250] 5-bromo-lH-pyrrolo[2, 3-b]ρyridine (6.Og, 30.45mmol) in ammonium hydroxide (12OmL) was treated with copper sulphate pentahydrate (1.50g, 6.09mmol, 0.2 eq) and heated in a sealed tube overnight. The reaction was diluted with EtOAc and the insoluble black solid was filtered off. The filtrate was extracted (EtO Ac/Water) and the organic layer washed with saturated aqueous ammonium chloride, followed by water and brine. The organics were dried over magnesium sulphate, filtered and evaporated to dryness to give the product as a pale brown solid (2.57g, 63percent)

Molecular Weight:133.15
XLogP3:0.6
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Exact Mass:133.063997236
Monoisotopic Mass:133.063997236
Topological Polar Surface Area:54.7
Heavy Atom Count:10
Complexity:126
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes